Best Vacation Homes in Freeport
New
House
4 Bedrooms
6 Baths
13 Guests
Private Pool
Fireplace/Heating
Pool
Balcony/Terrace
US $526/Night
7 Nights - US $3,684
House
10.0(3 Reviews)
4 Bedrooms
3 Baths
15 Guests
2873.96 ft²
- Balcony/Terrace
Pet Friendly
Parking
Air Conditioner
US $248/Night
7 Nights - US $1,736
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
Spa- Fireplace/Heating
- Pool
- Pet Friendly
US $278/Night
7 Nights - US $1,946
Cottage
10.0(7 Reviews)
1 Bedroom
1 Bath
4 Guests
600 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
View
US $191/Night
7 Nights - US $1,340
House
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
1593.06 ft²
Oceanfront- Ocean View
- View
- Pet Friendly
US $175/Night
7 Nights - US $1,225
Cottage
10.0(6 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
Kitchen- Parking
- Air Conditioner
US $154/Night
7 Nights - US $1,078
Cottage
10.0(5 Reviews)
2 Bedrooms
1 Bath
6 Guests
640 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $157/Night
7 Nights - US $1,100
House
10.0(4 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Air Conditioner
Internet
Child Friendly
US $180/Night
7 Nights - US $1,257
Freeport Luxury Rentals
House
10.0(4 Reviews)
10 Bedrooms
10 Baths
20 Guests
9000 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $1,913/Night
7 Nights - US $13,390
House
7.6(5 Reviews)
7 Bedrooms
6 Baths
20 Guests
7000 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $1,428/Night
7 Nights - US $9,998
Cottage
3 Bedrooms
1 Bath
8 Guests
1195 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $792/Night
7 Nights - US $5,546
House
9.8(10 Reviews)
4 Bedrooms
3 Baths
14 Guests
5000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $642/Night
7 Nights - US $4,496
Cottage
10.0(3 Reviews)
3 Bedrooms
3 Baths
12 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $539/Night
7 Nights - US $3,773
House
5.5(2 Reviews)
4 Bedrooms
4 Baths
14 Guests
5005.22 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
US $482/Night
7 Nights - US $3,374
House
9.8(31 Reviews)
4 Bedrooms
3 Baths
15 Guests
Hot Tub- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $471/Night
7 Nights - US $3,298
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $449/Night
7 Nights - US $3,144
Freeport Pet Friendly Vacation Rentals
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $153/Night
7 Nights - US $1,069
House
10.0(1 Review)
3 Bedrooms
1 Bath
8 Guests
1194.79 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Air Conditioner
US $78/Night
7 Nights - US $546
Cottage
9.8(11 Reviews)
2 Bedrooms
1 Bath
6 Guests
640 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $157/Night
7 Nights - US $1,100
Apartment
9.0(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
796.53 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $159/Night
7 Nights - US $1,114
Cottage
9.8(7 Reviews)
2 Bedrooms
1 Bath
6 Guests
640 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $138/Night
7 Nights - US $969
Cottage
9.6(8 Reviews)
2 Bedrooms
1 Bath
6 Guests
640 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $157/Night
7 Nights - US $1,100
Cottage
9.4(13 Reviews)
2 Bedrooms
1 Bath
6 Guests
640 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $157/Night
7 Nights - US $1,100
Cottage
8.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
640 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $134/Night
7 Nights - US $938
Freeport Large Vacation Homes
House
6.8(8 Reviews)
4 Bedrooms
2 Baths
17 Guests
1780 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $330/Night
7 Nights - US $2,308
House
8.6(5 Reviews)
4 Bedrooms
2 Baths
16 Guests
1980.56 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $365/Night
7 Nights - US $2,555
House
9.6(58 Reviews)
3 Bedrooms
3 Baths
10 Guests
1800 ft²
- Fireplace/Heating
- Ocean View
Lake View- Balcony/Terrace
US $380/Night
7 Nights - US $2,657
Apartment
5 Bedrooms
3 Baths
6 Guests
941.85 ft²
- Air Conditioner
- Internet
- Child Friendly
Wellness Facilities
US $276/Night
7 Nights - US $1,931
House
8.0(2 Reviews)
5 Bedrooms
3 Baths
15 Guests
2872 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $351/Night
7 Nights - US $2,458
House
4.8(15 Reviews)
4 Bedrooms
3 Baths
12 Guests
2800 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Child Friendly
US $400/Night
7 Nights - US $2,800
House
10.0(15 Reviews)
4 Bedrooms
3 Baths
14 Guests
5000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $347/Night
7 Nights - US $2,431
House
10.0(1 Review)
5 Bedrooms
2 Baths
6 Guests
1761 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $354/Night
7 Nights - US $2,477
Why Choose Rent By Owner for your Freeport Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Freeport
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here ensures you enjoy the region’s most favorable weather and local events, making your stay in this destination truly memorable and enhancing your experience with dependable vacation rentals.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warm weather ideal for beach outings and outdoor activities in this coastal region.
Average Temperature Daytime: 85°F to 90°F - Nighttime: 75°F to 80°F
Spring (March to May)
Springtime offers pleasant temperatures and blooming scenery, making it a popular period for exploring the area’s natural beauty and relaxing by the water.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
Off-Season Highlights
Fall (September to November)
In fall, the region experiences milder temperatures with fewer visitors, providing a tranquil setting for your stay while still enjoying comfortable weather.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 55°F to 65°F
Winter (December to February)
Winter offers cooler yet mild conditions, perfect for avoiding crowds and enjoying a peaceful retreat in this inviting destination.
Average Temperature Daytime: 60°F to 68°F - Nighttime: 45°F to 55°F
Weekly Weather Forecast for Freeport
How to Book Your Freeport Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Freeport
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor swimming pools available at some properties in the area.
- Relax on private or shared patios and decks with scenic views of the surroundings.
- Make use of outdoor grilling areas for family cookouts and gatherings.
- Take advantage of spacious yards perfect for outdoor games and activities.
- Explore nearby walking or biking paths that allow you to experience the local scenery.
- Benefit from access to outdoor seating areas ideal for relaxing and soaking up the sun.
- Discover community tennis courts or other shared sports amenities available in select rentals.
Top Attractions Around Freeport
What attractions are nearby?
Within this area, you can enjoy a variety of outdoor activities such as exploring pristine beaches, engaging in water sports, or discovering local nature trails, making your stay here both relaxing and adventurous.
Family Activities
- Hemingway's House Tour: Discover the rich literary history and charming architecture that make this local landmark a family favorite in the area.
- Gulf Coast Nature Exploration: Explore the scenic trails and natural beauty of nearby state parks, perfect for outdoor adventures with your loved ones.
- Local Farmers Market: Experience the vibrant community atmosphere while browsing fresh produce and handmade crafts in the region's bustling market.
- Beach Day at Freeport’s Shores: Enjoy a relaxing day building sandcastles and swimming in the calm waters just minutes from your vacation rental here.
Adult Activities
- Exploring the Beaches: Spend your day relaxing or taking a stroll along the pristine shores, enjoying the tranquil waters and soft sands that make this destination ideal for beach lovers.
- Wildlife Viewing at Local Preserves: Discover native flora and fauna through guided tours or self-led explorations at nearby nature preserves, offering a peaceful retreat within the region's natural beauty.
- Fishing Adventures: Cast your line in the productive waters here, whether from the shore or on a charter boat, to experience some of the region’s top fishing opportunities.
- Shopping and Dining: Indulge in local flavors and browse unique shops in charming downtown areas, perfect for immersing yourself in the area's cultural and culinary scene.
Other Places to Stay in Freeport, FL
Choctaw Beach
Freeport Travel Tips
How Can You Make the Most of Your Stay?
- Explore local beaches: Take advantage of the region’s pristine coastal areas by visiting nearby beaches to relax and enjoy the scenic views that make this destination unique.
- Visit regional dining spots: Savor authentic flavors at local eateries to experience the true taste of the area during your stay.
- Plan outdoor activities: Engage in outdoor pursuits like fishing, boating, or nature walks that showcase the natural beauty of this region.
- Choose well-located vacation rentals: Select accommodations close to the area's main attractions for convenient access and a more enjoyable vacation experience.
Transportation Options
- Rental Cars: Renting a car in the area offers you flexibility to explore Freeport and its surrounding attractions at your own pace.
- Public Transportation: Local bus services provide convenient access around this destination, making it easy to get around without a personal vehicle.
- Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available for quick and reliable transportation within this part of Florida.
- Shuttle Services: Shuttle transfers are available for popular destinations nearby, offering an efficient way to travel between your accommodation and key spots in this region.
Local Customs Options
- Respect for the Seafood Industry: Locals take pride in their seafood traditions, and you’ll notice this through their daily routines and local eateries emphasizing fresh catch.
- Beach Etiquette: When visiting the beaches here, it's customary to keep noise levels down and ensure your belongings don't obstruct access for others.
- Community Events and Festivals: Participating in or attending local festivals is a cherished way to connect with the area's culture and support small businesses.
- Environmental Conservation: Residents value the region’s natural beauty and encourage visitors to practice eco-friendly habits, such as proper waste disposal and respecting wildlife.
Frequently Asked Questions About Freeport?
1. What are the top vacation rentals in Freeport?
There are a lot of options in Freeport. If you plan on staying in the Freeport area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Freeport:
- (Sleeps 7) 3 bedroom/2 bath BRING YOUR BOAT/WAVERUNNERS-Lots of Parking Space
- Serene Home with PRIVATE Pool - Near Beaches - Dog Friendly - Firepit&Large Yard
- Cozy Cottage - King Bed - Close to Beaches - Dog Friendly - Firepit - Backporch
- Charming cottage in Freeport near the beaches. Enjoy your stay
- Short drive to the beautiful 30-A beaches!nCozy Riverwalk Landing Cottage 5-E
- Bay-Front Dream Mansion and Guest House -20 minutes to Destin beaches on 4 acres
- Your luxury suite in Choctaw Beach!
- Historical converted tavern surrounded by water, fabulous views, private dock.
- Bayfront Breeze
- Family retreat on the Bay near 30a at Casa de Bahia
2. How many vacation rentals have private pools in Freeport?
There are 1 vacation rentals with private pools near Freeport. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Freeport are best for families?
If you are looking for a family-friendly vacation home in Freeport, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Freeport:
4. How many Rentbyowner vacation rentals are available in Freeport?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 77 in the Freeport area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Freeport.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by property, so it's important to review the specific listing details. Many properties offer flexible or moderate cancellation options, but you should contact the host directly or check the listing for exact terms.
6. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning fees, service charges, or security deposits are typically outlined in the listing. Be sure to read the full property description to understand all costs before confirming your reservation.
7. How do I find the best vacation rentals in this region that fit my travel needs?
To find the ideal property, filter your search based on your preferred amenities, price range, and stay duration. Reading reviews and viewing photos can also help ensure the rental meets your expectations.
8. What security measures are in place for vacation rentals in this destination?
Security features vary by property, including secure locks, keyless entry, and surveillance cameras. Contact the host if you have specific concerns or need detailed information about safety measures.
9. Can I customize my stay or request special arrangements for my vacation rental here?
Many hosts are willing to accommodate special requests, such as early check-in, late check-out, or specific amenities. It's best to communicate your needs directly with the host through the booking platform.
Freeport Top Rated Vacation Rentals
House
10.0(26 Reviews)
3 Bedrooms
2 Baths
8 Guests
1183 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $256/Night
7 Nights - US $1,794
House
10.0(11 Reviews)
3 Bedrooms
2 Baths
8 Guests
1050 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $369/Night
7 Nights - US $2,581
Cottage
10.0(1 Review)
2 Bedrooms
1 Bath
6 Guests
640 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $167/Night
7 Nights - US $1,168
House
9.8(16 Reviews)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
- Fireplace/Heating
- Pool
- View
- Kitchen
US $225/Night
7 Nights - US $1,572
Cottage
9.6(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
640 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $157/Night
7 Nights - US $1,100
Cottage
9.6(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
640 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $146/Night
7 Nights - US $1,023
Other
9.3(67 Reviews)
26 Bedrooms
4 Baths
16 Guests
398.26 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $202/Night
7 Nights - US $1,412
House
8.6(4 Reviews)
3 Bedrooms
3 Baths
7 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $373/Night
7 Nights - US $2,610
